Fatty acid ethyl esters: Potentially toxic products of myocardial ethanol metabolism

Journal of Molecular and Cellular Cardiology

Volumn 30, Issue 11, 1998, Pages 2487-2494

  Beckemeier, Mary E ^a   Bora, Puran S ^a,b,c  

^a VETERANS AFFAIRS MEDICAL CENTER   (United States)

^b S LOUIS UNIV HLTH SCIENCES CENTER   (United States)

^c Saint Louis Medical Center   (United States)

Author keywords

Alcohol; Cardiomyopathy; Fatty acids; Metabolism; Mitochondria; Nonoxidative

Indexed keywords

ALCOHOL; FATTY ACID ESTER; SYNTHETASE;

ALCOHOL ABUSE; ALCOHOL CONSUMPTION; ALCOHOL METABOLISM; ALCOHOLIC CARDIOMYOPATHY; ARTICLE; ENZYME PURIFICATION; HEART MUSCLE; HUMAN; OXIDATION; PRIORITY JOURNAL;

EID: 0032212902     PISSN: 00222828     EISSN: None     Source Type: Journal    
DOI: 10.1006/jmcc.1998.0812     Document Type: Article

References (58)

1. ANDERSON B, WAAGSTEIN F, 1993. Spectrum and outcome of congestive heart failure in a hospitalized population. Am Heart J 126: 632-640.
2. ALEXANDER CS, 1967. Electron microscopic observations in alcoholic heart disease. B Heart J 29: 200-206.
3. ASOKAN S, FRANK M, WITHAM A, 1972. Cardiomyopathy without cardiomegaly in alcoholics. Am Heart J 84: 13-18.
4. BING RJ, TILLMANNS H, FAUVEL JM, SEELER K, MAO JC, 1974. Effect of prolonged alcohol administration on calcium transport in heart muscle of the dog. Circ res 35: 33-38.
5. BORA PS, BORA NS, WU X, LANGE LG, 1991. Molecular cloning, sequencing and expression of human myocardial fatty acid ethyl ester synthase-III cDNA. J Biol Chem 266: 12670-12673.
6. BORA PS, FARRAR MA, MILLER DD, CHAITMAN BR, GURUGE BL, 1996. Myocardial cell damage by fatty acid ethyl esters. J Cardiovascular Pharmacol 27: 1-6.
7. BORA PS, GURUGE BL, MILLER DD, CHAITMAN BR, FORTSON W, 1997. Human fatty acid ethyl ester synthase-III gene: genomic organization, nucleotide sequencing and chromosomal localization. Mol Cell Biochem 173: 145-151.
8. BORA PS, GURUGE BL, MILLER DD, CHAITMAN B, RUYLE M, 1996b. Purification and characterization of human heart fatty acid ester synthase/carboxylesterase. J Mol Cell Cardiol 28: 2027-2032.
9. BORA PS, LANGE LG, 1991a. Fatty acid ethyl ester, alcohol and liver changes. Alcohol and Drug Abuse Reviews II: 150-165.
10. BORA PS, LANGE LG, 1990. Fatty acid ethyl esters and heart disease. Alcohol Health Res World 14: 285-288.
11. BORA PS, LANGE LG, 1991b. Homogenous synthase-I from human myocardium is a glutathione S-transferase. Ann New York Acad Sci 625: 827-829.
12. BORA PS, SPILBURG C, LANGE LG, 1989a. Identification of a satellite fatty acid ethyl ester synthase from human myocardium as a glutathione S-transferase. J Clin Invest 84: 1942-1946.
13. BORA SP, SPILBURG C, LANGE LG, 1989b. Purification of homogeneity and characterization of major fatty acid ethyl ester synthase from human myocardium. FEBS Lett 258: 236-239.
14. BORA PS, SPILBURG C, LANGE LG, 1989c. Metabolism of ethanol and carcinogens by glutathione transferases. Proc Natl Acad Sci USA 86: 4470-4473.
15. BORA PS, SPILBURG C, LANGE LG, 1992a. Purification and characterization of fatty acid ethyl ester synthase-II from human myocardium. J Biol Chemistry 267: 13217-13221.
16. BORA PS, WU X, LANGE LG, 1992b. Site-specific mutagenesis of two histidine residues in fatty ethyl ester synthase-III. Biochem Biophys Res Commun 184: 706-711.
17. BORSTR, LOOS JA, CHRIST EF, SLATER EC, 1962. Uncoupling activity of long chain fatty acids. Biochem Biophys Acta 62: 509-517.
18. BURCH GE, DEPASQUALE NP, 1971. Alcohol cardiomyopathy. Am J Med 50: 141-146.
19. CLONINGER C, BOHMAN M, SIGVARDSSON D, 1981. Inheritance of alcohol abuse. Cross-fostering analysis of adopted men. Arch Gen Psychiatry 38: 861-868.
20. DOYLE KM, BIRD DA, AL-SALIHI S, HALLAQ Y, CLUETTE-BROWN JE, GOOS KA, LAPOSATA M, 1994. Fatty acid ethyl esters are present in human serum after ethanol ingestion. j Lipid Res 35: 428-437.
21. ETTINGER PO, LYONS M, OLDEWURTEL HA, REGAN TJ, 1976. Cardiac conduction abnormalities produced by chronic alcoholism. Am Heart J 91: 66-78.
22. GILLIGAN S, CLONINGER R, LANGE LG, 1989. Segregation of fatty acid ethyl ester synthase gene. Am J Human Genet 46: 145-150.
23. GIMENO AL, GIMENO MF, WEBB JL, 1962. Effects of ethanol on cellular membrane potentials and contractility of isolated rat atrium. Am J Physiol 203: 194-196.
24. GOLDSTEIN D, 1983. The pharmacology of alcohol. Oxford University Press, New York.
25. GOODWIN D, 1987. Genetic factors in the development of alcoholism. Adv Intern Med 31: 383-398.
26. GORSKI NP, NOURALDIN H, DUBE DM, PREFFER FI, DOMBKOWSKI DM, VILLA EM, LEWANDROWSK KB, WEISS RD, HUFFORD C, LAPOSATA M, 1996. Reduced fatty acid ethyl ester synthase activity in the white blood cells of alcoholics. Alcohol Clin Exp Res 20: 268-274.
27. HABER PS, WILSON JS, APTE MV, PIROLA RC, 1993. Fatty acid ethyl esters increase rat pancreatic lysosomal fragility. J Lab Clin Med 121: 759-764.
28. HAMAMOTO T, YAMADA S, HIRAYAMA C, 1990. Non-oxidative metabolism of ethanol in the pancreas; implication in alcoholic pancreatic damage. Biochem Pharmacol 39: 241-245.
29. HAMAMOTO T, YAMADA S, MURAWAKI Y, KAWASAKI H, 1991. Effect of ethanol feeding on fatty acid ethyl ester synthase in the liver and pancrease of rats fed a nutritionally adequate diet or a low protein diet. Biochem Pharmacol 42: 1148-1150.
30. HASTILLO AH, POLAND J, HESS ML, 1980. Mechanical and subcellular function of rat myocardium during chronic ethanol consumption. Proc Soc Exp Biol Med 164: 415-420.
31. HIBBS RG, FERRANS VJ, BLACK WC, WEILBAECHER DG, WALSH JJ, BURCH GE, 1965. Alcoholic Cardiomyopathy. Am Heart J 69: 766-779.
32. HUNGUND BL, GOLDSTEIN DB, VILLEGAS F, COOPER CP, 1988. Formation of fatty acid ethyl esters during chronic ethanol treatment in mice. Biochem Pharmacol 37: 3001-3004.
33. JEZEK P, FREISLEBEN HJ, 1994. Fatty acid binding site of the mitochondrial uncoupling protein. Demonstration of its existence by EPR spectorscopy of 5-doxyl-stearic acid. FEBS Lett 343: 22-26.
34. KUPARI M, KOSKINEN P, SUOKAS A, 1991. Left ventricular size, mass and function in relation to the duration and quantity of heavy drinking in alcoholics. Am J Cardiol 67: 274-279.
35. LANGE LG, BERGMAN SR, SOBEL BE, 1981. Identification of fatty acid ethyl esters as products of rabbit myocardial ethanol metabolism. J Biol Chem 256: 12968-12973.
36. LANGE LG, 1982. Nonoxidative ethanol metabolism. Formation of fatty acid ethyl esters by cholesterol esterase. Proc Natl Acad Sci, USA 79(13): 3954-3957.
37. LANGE LG, SOBEL BE, 1983a. Mitochondrial dysfunction induced by fatty acid ethyl esters, myocardial metabolites of ethanol. J Clin Invest 72: 724-731.
38. LANGE LG, SOBEL BE, 1983b. Mitochondrial metabolites of ethanol. Circulation Research 52: 479-482.
39. LAPOSATA EA, LANGE LG, 1986. Presence of non-oxidative ethanol metabolism in human organs commonly damaged by ethanol abuse. Science 231: 497-499.
40. LAPOSATA EA, SCHERRE DE, MAZOW ?, LANGE LG, 1987. Metabolism of ethanol by human brain to fatty acid ethyl esters. J Biol Chem 262: 4653-4657.
41. LOPASCHUK GD, BELKE DD, GAMBLE J, ITOI T, SCHONEKESS BO, 1994. Regulation of fatty acid oxidation in the mammalian heart in health and disease. Biochimica Biophysica Acta 1213: 263-276.
42. MANNERVIK B, ALIN P, GUTHENBERG C, JENSSON H, TAHIR MK, WARHOLM M, JORNVALL H, 1985. Identification of the three class of cytosolic glutathione S-transferase common to several mammalian species: correlation between structural data and enzymatic properties. Proc Natl Acad Sci, USA 82: 7202-7206.
43. MOGELSON S, LANGE LG, 1984. Nonoxidative ethanol metabolism in rabbit myocardium: Purification to homogeneity of fatty acid ethyl ester synthase. Biochemistry 23: 4075-4081.
44. MOGELSON S, PIEPER SJ, LANGE LG, 1984. Thermodynamic bases for fatty acid ethyl ester synthase catalyzed esteriflcation of free fatty acid ethyl esters. Biochemistry 23: 4082-4087.
45. NOREN GR, STANLEY NA, EINZIG S, MIKELL FL, ASINGER RW, 1983. Alcohol-induced congestive cardiomyopathy: an animal model. Cardiovasc Res 17: 81-8 7.
46. PACHINGER OM, TILLMANNS H, MAO JC, FAUVEL JM, BING RJ, 1973. The effect of prolonged administration of ethanol on cardiac metabolism and performance in the dog. J Clin Invest 52: 2690-2696.
47. PIANO MR, DORIE SW, 1994. Alcoholic heart disease: a review. Heart Lung 23: 3-17.
48. REGAN TJ, LEVINSON GE, OLDEWURTEL HA, FRANK MJ, WEISSE AB, MOSCHOS CB 1969. Ventricular function in noncardiacs with alcoholic fatty liver: role of ethanol in the production of cardiomyopathy. J Clin Invest 48: 397-407.
49. ROBERTS WC, SIEGEL RJ, MCMANUS BM, 1987. Idiopathic dilated cardiomyopathy: analysis of 152 necropsy patients. Am J Cardiol 60: 1340-1355.
50. SARMA JSM, IKEDA S, FISCHER R, MARUYAMA Y, WEISHAAR R, BING RJ, 1976. Biochemical and contractile properties of heart muscle after prolonged alcohol administration. J Mol Cell Cardiol 8: 951-972.
51. SEGAL LD, RENDIG SV, CHOQUET Y, CHACKO K, AMSTERDAM EA, MASON DT, 1975. Effects of chronic graded ethanol consumption on the metabolism ultrastructure and mechanical function of the rat heart. Cardiovasc Res 9: 649-663.
52. ++ flux dysfunctions are reversible. J Mol Cell Cardiol 13: 443-455.
53. SMITH CM, BORA PS, BORA NS, JONES C, GERHARD DS, 1995. Genetic and radiation-reduced somatic cell hybrid sublocation of the human GSTP1 gene. Cyto Cell Genet 71: 235-239.
54. SZCZEPIORKOWSKI ZM, DICKERSIN RG, LAPOSATA M, 1995. Fatty acid ethyl ester decreases human hepatoblastoma cell proliferation and protein synthesis. Gastroenterology 108: 515-522.
55. TSUJITA T, OKUDA H, 1992. Fatty acid ethyl ester synthase in rat adipose tissue and its relationship to carboxylesterase. J Biol Chem 267: 23489-23494.
56. URBANO-MARQUEZ A, ESTRUCH R, NAVARRO-LOPEZ F, GRAU JM, MONT L, RUBIN E, 1989. The effects of alcoholism on skeletal and cardiac muscle. N Engl J Med 320: 409-416.
57. VIKHERT AM, TSIPLENKOVA VG, CHERPACHENKO NM, 1986. Alcoholic cardiomyopathy and sudden cardiac death. J Am Coll Cardiol 8: 3A-11A.
58. +)-activated adenosine triphosphatase activity of cardiac plasm membranes. Biochem Pharmacol 24: 27-32.